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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middletown vacation homes

A cozy room with a bed, a sofa, a table, and chairs.

1. Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (4 reviews)
"Good place was very happy"
United States
Randy B.
The price is ￥14,623
￥31,313 total
includes taxes & fees
Aug 31 - Sep 1
Emerald Lodge quiet efficiency
A covered porch with two grey upholstered chairs and a small table, wooden railings, and a window with a curtain.

2. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is ￥20,187
￥43,076 total
includes taxes & fees
Sep 9 - Sep 10
Tangerine Cottage spacious home
A wooden deck with a red door, a small window, and a sign indicating a 'Guesthouse Cottage'.

3. Stagecoach Cottage quiet efficiency

Stagecoach Cottage quiet efficiency
Middletown
The price is ￥15,895
￥32,744 total
includes taxes & fees
Aug 30 - Aug 31
Stagecoach Cottage quiet efficiency

4. 15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18

15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18
Middletown
The price is ￥119,451
￥251,809 total
includes taxes & fees
Sep 7 - Sep 8
15-Acre Gated Wine Country Estate and 7BR Mansion, Pool, Spa ,Sleeps 18

5. Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views

Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
Clearlake Oaks
The price is ￥27,180
￥59,758 total
includes taxes & fees
Aug 31 - Sep 1
Hilltop Hideaway: 4 acres, Hot Tub, Stunning Views
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

6. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (30 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is ￥12,732
￥30,099 total
includes taxes & fees
Sep 7 - Sep 8
Cobb Mountain Chalet King Size Suite
A wooden deck leading to a building with a large window overlooking a lake and hills.

7. Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is ￥21,172
￥31,979 total
includes taxes & fees
Aug 25 - Aug 26
Bungalow on the lake
A wooden pathway leading to a house with a view of a lake and mountains.

8. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
Clearlake
7.4 out of 10, Good, (3 reviews)
"Nice little house on the lake. Is a cabin style house for sure. Host is awesome great communication and makes sure u have what u need.Will return for sure."
United States
Arlen H.
The price is ￥20,664
￥44,255 total
includes taxes & fees
Aug 25 - Aug 26
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A view of a lake with trees in the foreground and hills in the background.

9. Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Clearlake Oaks
8.4 out of 10, Very Good, (13 reviews)
"Great communication from the property owner! Easy stay, well-appointed for our brief stay - beautiful lake views, sunsets, and sunrise!"
United States
Melanie B.
The price is ￥23,843
￥40,851 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
A swimming pool with a slide, a barbecue area, and a wooden deck.

10. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (27 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is ￥19,885
￥44,969 total
includes taxes & fees
Aug 27 - Aug 28
2 Hidden Wine Country Gem Upstairs Unit
A hallway with wooden walls and a blue door, leading to a room with a bed and a table.

11. Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (21 reviews)
"Beautiful view from the deck! Wind was blowing the tree in the evening and it was so peaceful. House had everything you could need."
United States
tabatha p.
The price is ￥14,162
￥33,943 total
includes taxes & fees
Sep 2 - Sep 3
Cobb Mountain Chalet Main Floor
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

12. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥26,227
￥57,953 total
includes taxes & fees
Aug 31 - Sep 1
Wine Country Cottage Escape
A wooden deck with outdoor furniture, a pool, and a view of a marina and hills.

13. Waterfront Luxury- 3 Plus Bedrooms

Waterfront Luxury- 3 Plus Bedrooms
Clearlake Oaks
9.4 out of 10, Exceptional, (26 reviews)
"The comfort and privacy"
United States
Beverly D.
The price is ￥22,253
￥54,615 total
includes taxes & fees
Sep 15 - Sep 16
Waterfront Luxury- 3 Plus Bedrooms
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

14. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (74 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
Wine Country Farmhouse with Hot Tub
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

15. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is ￥24,637
￥128,965 total
includes taxes & fees
Sep 1 - Sep 2
Wildflower
A waterfront property with multiple buildings, a dock, and a palm tree.

16. Lakefront, 1 King Bed, dock, mist view, electronic firepit

Lakefront, 1 King Bed, dock, mist view, electronic firepit
Lower Lake
10.0 out of 10, Exceptional, (2 reviews)
"Host was very welcoming and we had many amenities, including the dock, movies, and foosball. Overall, enjoyed the stay very much. Minor issues existed but were resolved fairly quickly"
United States
Vishnu N.
The price is ￥65,952
￥122,858 total
includes taxes & fees
Aug 25 - Aug 26
Lakefront, 1 King Bed, dock, mist view, electronic firepit
A modern kitchen with stainless steel appliances, grey cabinets, and a marble backsplash.

17. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is ￥95,418
￥120,062 total
includes taxes & fees
Aug 25 - Aug 26
The Parlour House at the Fainting Couch
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

18. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is ￥29,724
￥66,810 total
includes taxes & fees
Sep 21 - Sep 22
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

19. Modern Organic 3BR Oasis w/ Creek&Near State Park

Modern Organic 3BR Oasis w/ Creek&Near State Park
Kenwood
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is ￥31,094
￥88,286 total
includes taxes & fees
Aug 25 - Aug 26
Modern Organic 3BR Oasis w/ Creek&Near State Park
A wooden deck with a red umbrella, white lounge chairs, and a view of a calm lake with mountains in the background.

20. The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks

The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Kelseyville
9.8 out of 10, Exceptional, (85 reviews)
"Great place i loved the backyard. Stargazing and fishing. Wish had more time to explore the lake by boat. I highly recommend this place."
United States
Richard M.
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"Staff is very helpful!"
Rachel 2-night trip
Posted 2 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
240
Accommodation
597 Vacation Homes
Lowest Price
￥30,099
Highest Price
￥251,809